Luxury Vacation Home Rentals on Anna Maria Island

Discover our Anna Maria Island vacation rentals with private pools, perfect for relaxing getaways with family, friends, or pets. From Anna Maria to Holmes Beach, Bradenton Beach, & right Off Island, our homes offer privacy, comfort, and easy access to the island’s best beaches, shops, and restaurants.

Our local team is here to ensure a seamless stay, offering personalized support and insider tips to make your vacation unforgettable. Whether you’re bringing your pup  or planning a family retreat, you’ll find the ideal home for your island escape.

Properties Available 41 properties available
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl East*Discover Island Girl East, a bright coastal retreat just five houses from the beach. Here, mornings begin with the sound of swaying palms, and afternoons drift between the pool and the sea.
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Island Girl East
Island Girl East
Holmes Beach
$205.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4 (3)
Welcome to Family Tides – Unit A!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides A (Bottom Unit)*Located just steps from the Gulf of Mexico and walkable to Bridge Street, this ground-level unit invites you to unwind, connect, and enjoy a thoughtfully
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Family Tides - A
Family Tides - A
Bradenton Beach
$42.00 - $993.60 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Three Little Birds!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep into Three Little Birds — a bright, joyful island home designed for gathering, connecting, and letting the days unfold naturally. With Gulf views, a privat
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Three Little Birds
Three Little Birds
Anna Maria
$800.00 - $2,145.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (2)
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience AMI Peppertree Paradise — a light-filled beach home where mornings begin with salt air and end beneath the glow of island skies.Just three houses from th
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AMI Peppertree Paradise
AMI Peppertree Paradise
Anna Maria
$360.00 - $935.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (6)
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units: Island Girl East & Island Girl West*The SpaceWith room for up to 10 guests, Island Girl East & West is thoughtfully designed for shared experiences and easy island living. Each side of t
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Island Girl - East & West
Island Girl - East & West
Holmes Beach Pet Friendly
$305.00 - $780.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (6)
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceSet between the Gulf of Mexico and the Intracoastal Waterway, Mariner’s Crossing offers balance — connection and privacy, activity and calm. With
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Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$800.00 - $3,850.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (14)
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
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Kokomo
Kokomo
Holmes Beach
$255.00 - $680.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi
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Tern Key
Tern Key
Anna Maria
$900.00 - $2,035.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (12)
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please note: The home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.The SpaceEvery corner of Point’s H
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Point's Hideaway
Point's Hideaway
Anna Maria Pet Friendly
$350.00 - $902.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (8)
Welcome to Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Where gathering comes naturally and every generation finds its place in the sun.Just steps from the Gulf of Mexico in Bradenton Beach, this dual-home property offers
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Family Tides
Family Tides
Bradenton Beach
$450.00 - $1,836.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 4.9 (10)
Welcome to Sea La Vie!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere light dances across the water and modern design meets island ease, Sea La Vie invites you to experience the beauty of Anna Maria Island from a space that feels both lux
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Sea La Vie
Sea La Vie
Anna Maria
$510.00 - $1,760.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
Welcome to Family Tides – Unit BOn Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B (Top Unit)*Set above its sister unit in this beautiful duplex, this light-filled home offers space for connection and comfort, with access to shared outdoor amenities designed for
Hot HOT 23
Family Tides - B
Family Tides - B
Bradenton Beach
$280.00 - $993.60 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4 (1)

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When is the best time to visit Anna Maria Island?

Anna Maria Island is beautiful any time of year, but different seasons are best for different activities. Spring and fall both have warm temperatures and fewer crowds, and are perfect for a more relaxed vacation spent enjoying the outdoors and checking out local attractions. Summer is the hottest and busiest time of year. If you’re looking for exciting summer energy, summer is your best bet. Winter in Anna Maria Island has cooler temperatures and the lowest prices.

Are dogs allowed on the beaches in Anna Maria Island?

Most of the beaches on Anna Maria Island do not allow dogs, so it’s important to check the regulations before bringing your pup. But even if you can’t bring your four-legged family member to one of the main beaches, there are plenty of alternatives, like Palma Sola Causeway Park & Bayfront Park. View Pet Friendly Rentals in Anna Maria Island.

What are the best beaches on Anna Maria Island?

Every beach on the island is fantastic! We love Bean Point, on the northern tip of the island, for its views, wildlife viewing, and spectacular shelling. Bradenton Beach is great for anyone looking for a mix of relaxation and activities, with easy access to biking trails and restaurants. And Holmes Beach is lovely for anyone who wants to swim in clear waters or relax in the sugar-soft sands the island is famous for. Rentals within walking distance to the beach

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